Triptycene polymers and copolymers

ABSTRACT

The invention relates to conjugated polymers containing triptycene units. The polymers according to the invention are on the one hand homopolymers comprising a recurring unit containing a triptycenylene radical, and copolymers comprising two or more different recurring units, which may contain a triptycenylene radical or an arylene, heteroarylene, vinylene and ethynylene radical. The polymers according to the invention are employed as electroluminescent materials.

The invention relates to conjugated polymers and copolymers containingtriptycene moieties.

There is a considerable industrial demand for large-area solid-statelight sources for a number of applications, predominantly in the area ofdisplay elements, display-screen technology and illumination technology.The requirements made of these light sources cannot at present be met inan entirely satisfactory manner by any of the existing technologies.

As an alternative to conventional display and illumination elements,such as incandescent lamps, gas-discharge lamps andnon-self-illuminating liquid-crystal display elements,electroluminescent (EL) materials and devices, such as light-emittingdiodes (LEDs), have already been in use for some time.

Besides inorganic electroluminescent materials and devices,low-molecular-weight organic electroluminescent materials and deviceshave also been known for about 20 years (see, for example, U.S. Pat. No.3,172,862). Until recently, however, such devices were greatlyrestricted in their practical usability.

WO 90/13148 and EP-A-0 443 861 describe electroluminescent devices whichcontain a film of a conjugate polymer as light-emitting layer(semiconductor layer). Such devices offer numerous advantages, such asthe possibility of producing large-area, flexible displays simply andinexpensively. In contrast to liquid-crystal displays,electroluminescent displays are self-illuminating and therefore do notrequire any additional back-lighting source.

A typical device in accordance with WO 90/13148 consists of alight-emitting layer in the form of thin, dense polymer film(semiconductor layer) which comprises at least one conjugated polymer. Afirst contact layer is in contact with a first surface, a second contactlayer is in contact with a further surface of the semiconductor layer.The polymer film of the semiconductor layer has a sufficiently lowconcentration of extrinsic charge carriers so that, on application of anelectric field between the two contact layers, charge carriers areintroduced into the semiconductor layer, the first contact layer beingpositive relative to the other, and the semiconductor layer emittingradiation. The polymers used in such devices are conjugated. The termconjugated polymer is taken to mean a polymer which has a delocalizedelectron system along the main chain. The delocalized electron systemprovides the polymer with semiconductor properties and enables it totransport positive and/or negative charge carriers with high mobility.

The polymeric material for the light-emitting layer using WO 90/13148 ispoly(p-phenylenevinylene), and it is proposed to replace the phenylgroup in a material of this type by a heterocyclic or a fusedcarbocyclic ring system. In addition, poly(p-phenylene), PPP, is alsoused as electroluminescent material (G. Grem et al., Synth. Met. 1992,51, page 383).

Although good results have been achieved with these materials, the colorpurity, for example, is still unsatisfactory. Furthermore, it isvirtually impossible to generate blue or white emission with thepolymers disclosed hitherto.

Since, in addition, the development of electroluminescent materials, inparticular based on polymers, can in no way be regarded as complete, theproducers of illumination and display devices are interested in anextremely wide variety of electroluminescent materials for such devices.

One of the reasons for this is that only the interaction of theelectroluminescent materials with the other components of the devicesallows conclusions to be drawn on the quality of the electroluminescentmaterial too.

German Patent Application 197 44 792.9, which has an earlier prioritydate and was published before the priority date of the presentapplication, describes the use of triptycene derivatives aselectroluminescent materials. This application relates to the monomerictriptycene derivatives, which, in order to be used as electroluminescentmaterials, are applied in the form of a film to a substrate by knownmethods, such as dipping, spin coating, vapor deposition or bufferingout under reduced pressure.

The object of the present invention is to provide novel polymericelectroluminescent materials containing triptycene moieties which aresuitable, on use in illumination or display devices, for improving theproperty profile of these devices.

The object has been achieved by a conjugated polymer containing

a) from 1 to 100 mol % of at least one recurring unit RU1 of the generalformula (I)

—B—Tr—A—  (I)

 in which Tr is a triptycenylene radical of the general formula (II)

or of the general formula (III)

or of the general formula (IV)

where R¹ to R¹⁶=H, linear or branched C₁-C₂₂-alkyl or alkoxy, in whichone or more non-adjacent CH₂ groups may be replaced by —O—, —S—, —CO—,—COO—, —O—CO—, an amino or amide group and in which one or more H atomsmay be replaced by F atoms, or C₆-C₂₀-aryl or aryloxy, COOR, SO₃R, CN,halogen or NO₂,

where G, L and where appropriate G¹ and L¹=CR¹⁷, N, P, As, where R¹⁷=H,C₁-C₂₂-alkyl or alkoxy, where one or more non-adjacent CH₂ groups may bereplaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group andin which one or more H atoms may be replaced by F atoms, or C₆-C₂₀-aryl,halogen or CN,

A and B are a single bond, a vinylene radical which is optionallysubstituted by H, linear or branched C_(1-C) ₂₂-alkyl or alkoxy, inwhich one or more non-adjacent CH₂ groups may be replaced by —O—, —S—,—CO—, —COO—, —O—CO—, an amino or amide group and in which one or more Hatoms may be replaced by F atoms, or C₆-C₂₀-aryl or aryloxy,C₃-C₂₀-heteroaryl, COOR, SO₃R, CN, halogen, NO₂, amino, alkylamino ordialkylamino, or are an ethynylene radical, an arylene radical of thegeneral formula (V)

where R¹⁸ to R²¹ are as defined above for R₁ to R16,

a heteroarylene radical of the general formula (VI)

where X and Y=N or CR²², and Z=O, S, NR²³, CR²⁴R²⁵, CR²⁶=CR²⁷ orCR²⁸=N—, in which R²² to R²⁸ are as defined above for R¹ to R¹⁶, or aspirobifluorenylene radical of the general formula (VII)

where R²⁹ to R³² are as defined above for R¹ to R¹⁶, and

b) from 0 to 99 mol % of at least one recurring unit RU2 of the generalformula (VIII)

where R³³ to R³⁶ are as defined above for R¹ to R¹⁶, or of the generalformula (IX)

where X, Y and Z are as defined above, and D is a single bond, avinylene radical which is optionally substituted by H, linear orbranched C₁-C₂₂-alkyl or alkoxy, in which one or more non-adjacent CH₂groups may be replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino oramide group and in which one or more H atoms may be replaced by F atoms,or C₆-C₂₀-aryl or aryloxy, C₃-C₂₀-heteroaryl, COOR, SO₃R, CN, halogen,NO₂, amino, alkylamino or dialkylamino, or is an ethynylene radical.

In a preferred embodiment of the invention, L, G and where appropriateL¹ and G¹ are a CH group.

A and B are a single bond, an optionally substituted vinylene radical,an ethynylene radical, an optionally substituted arylene radical, anoptionally substituted heteroarylene radical or a spirobifluorenyleneradical.

Preferred substituted vinylene radicals are methylvinylene,phenylvinylene and cyanovinylene.

Particular preference is given to an unsubstituted vinylene radical.

Preferred arylene radicals are 1,4-phenylene, 2,5-tolylene,1,4-naphthylene, 1,9 antracylene, 2,7-phenantrylene and2,7-dihydrophenantrylene.

Preferred heteroarylene radicals are 2,5-pyrazinylene,3,6-pyridazinylene, 2,5-pyridinylene, 2,5-pyrimidinylene,1,3,4-thiadiazol-2,5-ylene, 1,3-thiazol-2,4-ylene,1,3-thiazol-2,5-ylene, 2,4-thiophenylene, 2,5-thiophenylene,1,3-oxazol-2,4-ylene, 1,3-oxazol-2,5-ylene and1,3,4-oxadiazol-2,5-ylene, 2,5-indenylene and 2,6-indenylene.

Methods for the synthesis of these monomers are based, for example, onthe synthesis of 9,9′-spirobifluorene, for example from 2-bromobiphenyland fluorenone via a Grignard synthesis, as described by R. G. Clarkson,M. Gomberg, J. Am. Chem. Soc. 1930, 52, page 2881, which is subsequentlyfurther substituted in a suitable manner.

Functionalizations of 9,9′-spirobifluorene are described, for example,in J. H. Weisburger, E. K. Weisburger, F. E. Ray, J. Am. Chem. Soc.1959, 72, 4253; F. K. Sutcliffe, H. M. Shahidi, D. Paterson, J. Soc.Dyers Colour 1978, 94, 306; and G. Haas, V. Prelog, Helv. Chim. Acta1969, 52, 1202.

The desired substitution pattern of the 9,9′-spirobifluorene monomer isobtained significantly more favorably if the spiro linkage is carriedout starting from suitably substituted starting materials, for examplewith 2,7-difunctionalized fluorenones, and the 2′,7′-positions which arestill free are then, if desired, further functionalized after build-upof the spiro atom (for example by halogenation or acylation, withsubsequent C—C linkage after conversion of the acetyl groups intoaldehyde groups, or by build-up of heterocycles after conversion of theacetyl groups into carboxylic acid groups).

The further functionalization can be carried out by methods known fromthe literature, as described in standard works on organic synthesis, forexample Houben-Weyl, Methoden der Organischen Chemie [Methods of OrganicChemistry], Georg-Thieme Verlag, Stuttgart, and in the correspondingvolumes of the series “The Chemistry of Heterocyclic Compounds” by A.Weissberger and E. C. Taylor (editors).

The substituted triptycene or heterotriptycene basic structures areaccessible by various synthetic routes. At this point, mention may bemade by way of example, but not in a restrictive manner, of thefollowing:

1. Syntheses from substituted anthracene (or substituted acridine orsubstituted phenazine) and decahydroaromatic compounds, for examplestarting from

a) substituted o-fluorobromofluorobenzenes with reactive metals, suchas, for example, magnesium, for example analogously to G. Wittig, Org.Synth. IV 1963, 964;

b) substituted o-dihalobenzenes and butyllithium with elimination ofmetal halide, for example analogously to H. Hart, S. Shamouilian, Y.Takehira J. Org. Chem. 46 (1981) 4427;

c) substituted monohalobenzenes and strong bases with elimination ofhydrogen halide, for example analogously to P. G. Sammes, D. J.Dodsworth, J. C. S. Chem. Commun. 1979, 33.

d) substituted anthranilic acid derivatives and isoamyl nitrile, forexample analogously to C. W. Jefford, R. McCreadie, P. Müller, B.Siegfried, J. Chem. Educ. 48 (1971) 708.

e) a review of the preparation of a series of substituted dehydroaromatccompounds is given in Houben-Weyl, Methoden der Organischen Chemie[Methods of OrganicChemistry], 4th Edition 1981, Volume V/2b, pp.615,Georg-Thieme-Veriag, Stuttgart.

2. Syntheses by deamination of substituted anthracene-9,10-imines, forexample analogously to L. J. Kricka, J. M. Vemon, J. C. S. Perkin I,1973, 766.

3. Synthesis by cycloaddition of substituted 1,4-quinones withsubstituted anthracene derivatives, for example analogously to E. Clar,Chem. Ber. 64 (1931) 1676; W. Theilacker, U. Berger-Brose, K. H. Beyer,Chem. Ber. 93 (1960) 1658; P. D. Bartlett, M. J. Ryan, J. Am. Chem. Soc.64 (1942) 2649; P. Yates, P. Eaton, J. Am. Chem. Soc. 82 (1960) 4436. V.R. Skvarchenko, V. K. Shalaev, E. I. Klabunovskii, Russ. Chem. Rev. 43(1974) 951;

Further syntheses of substituted triptycenes are given by way of examplein C. F. Wilcox, F. D. Roberts, J. Org. Chem. 30 (1965) 1959; T. H.Regan, J. B. Miller, J. Org. Chem. 32 (1967) 2798.

Further syntheses for heterotrypticenes are given, for example, in D.Hellwinkel et al., Chem. Ber. 111 (1978); or D. Hellwinkel et al.,Angew. Chem. 24 (1969) 1049; N. P. McCleland et al., J. Am. Chem. Soc.(1927) 2753; N.A.A. Al-Jabar et al., J. Organomet. Chem. 287 (1985) 57.

Bistriptycene basic structures or heterobistriptycene basic structuresare likewise accessible by various synthetic routes. Mention may be madeat this point by way of example of the following:

1) Syntheses from substituted anthracene (or substituted acridine orsubstituted phenazine) and substituted didehydrobenzenes, for exampleanalogously to H. Hart, S. Shamouilian, Y. Takehira J. Org. Chem. 46(1981) 4427;

2) Synthesis by cycloaddition of substituted anthracene derivatives with1,4-benzoquinone, for example analogously to E. Clar, Chem. Ber. 64(1931) 1676; P. Yates, P. Eaton, J. Am. Chem. Soc. 82 (1960) 4436; W.Theilacker, U. Berger-Broske, K. H. Beyer, Chem. Ber. 93 (1960) 1658.

Further syntheses are given by way of example in H. Hart et al.,Tetrahedron 42 (1986) 1641; V. R. Skvarchenko et al., Russ. Chem. Rev.43 (1974) 951; V. R. Skvarchenko et al., J. Org. Chem. USSR (Engl.trans.) 3 (1967) 1477.

In a preferred embodiment, the polymers according to the inventionconsist of precisely one type of recurring units RU1 (homopolymers).Particular preference is given to homopolymers in which A is selectedfrom the group consisting of 2,5-thiophenylene, 2,5-oxadiazolylene,1,4-phenylene, vinylene and ethynylene, and B is a single bond.

Preferred homopolymers are furthermore those in which A and B areidentical and are selected from the group consisting of2,5-thiophenylene, 1,4-phenylene, vinylene and ethynylene.

In a further preferred embodiment, the polymers according to theinvention comprise from 1 to 99 mol % of recurring units RU2(copolymers). The copolymers preferably comprise from 5 to 95 mol % ofrecurring units RU2, particularly preferably from 10 to 90 mol % ofrecurring units RU2.

Preferred copolymers are furthermore those in which A is a single bondand B is a single bond, a vinylene group or ethynylene group. Particularpreference is given to copolymers in which B is a vinylene group.

Preferred copolymers are furthermore binary copolymers comprisingrecurring units RU1 and recurring units RU2 of the general formula(VIII) or (IX).

Preferred copolymers are furthermore quatemary copolymers comprisingrecurring units RU1 and two types of recurring units RU2 of the generalformula (VIII) or (IX).

Particularly preferred copolymers are those in which the recurring unitsRU2 are recurring units of the general formula (VIII).

Particular preference is furthermore given to copolymers in which thegroup D in the general formulae (VIII) and (IX) is a vinylene group.

The polymers are prepared by conventional methods of polymerizationreaction, as described, for example, in “Makromoleküle” [Macromolecules]by Hans-Georg Elias (Hüthig & Wepf Verlag Basle-Heidelberg-New York) orin Houben-Weyl, Methoden der organischen Chemie [Methods of OrganicChemistry], Vol. XIV, Makromolekulare Stoffe [Macromolecular Substances](G. Thieme, Stuttgart, 1961 and 1963). The selection is in each casemade depending on the type of functionalization of the monomers and thedesired molecular weight.

Starting from the monomers obtained as described, the polymerization togive polymers according to the invention is possible by a plurality ofprocesses.

For example, halogen derivatives of the triptycenes can be polymerizedoxidatively (for example using FeCl₃, see, inter alia, P. Kovacic etal., Chem. Ber., 87, 1987, 357 to 379; M. Wenda et al., Macromolecules25, 1992, 5125) or electrochemically (see, inter alia, N. Saito et al.,Polym. Bul. 30, 1993, 285).

Polymers according to the invention can likewise be prepared fromdihalogen derivatives by polymerization with copper/triphenylphosphinecatalysis (see, for example, G. W. Ebert et al., J. Org. Chem. 1988, 53,4829, or nickel/triphenylphosphine catalysis (see, for example, H.Matsumoto et al., J. Org. Chem. 1983, 48, 840).

Aromatic diboronic acids and aromatic dihalides or aromatic haloboronicacids can be polymerized with palladium catalysis (Suzuki coupling)(see, for example, M. Miyaura et al., Synth. Commun. 11, 1981, 513; R.B. Miller et al., Organometallics 3, 1984, 1261). In a similar manner,aromatic distannanes and aromatic dihalides can be polymerized (see, forexample, J. K. Stille, Angew. Chem. Int. Ed. 25,1986, 508).

Furthermore, dibromoaromatic compounds can be converted into dilithio ordi-Grignard compounds. These can then be polymerized with furtherdihaloaromatic compounds by means of CuCl₂ (see, for example, G. Wittiget al., Liebigs Ann. Chem. 704, 91,1967; H. A. Stabb et al., Chem. Ber.100, 1967, 293 and T. Kaufmann, Angew. Chem. 86,1974, 321).

Particular methods are necessary for the preparation ofpoly(triptycenyl-vinylenes), which are likewise according to theinvention. Thus, the synthesis can be carried out, for example, bypolycondensation of para-dihalomethyl-substituted triptycenederivatives. The polymerization here is carried out in a suitablesolvent by addition of base (see, for example, H.Hörhold et al.,Makromol. Chem, Macromol. Symp. 12, 1987, 229-258). Precursorpolymerization is likewise possible; in this case, apoly(triptycenylene-vinylene) is prepared by elimination of a precursorradical present (for example CH₂S⁺R₂) by heat treatment or basetreatment (see, for example, R. A. Wessling, J. Polym. Sci; Polym. Sym.72, 1985, 55-66).

Further ways of preparing poly(triptycenylenes) are, for example, Homerpolymerization and Wittig polymerization. In these, two types of monomer(aldehydes with phosphonates (Homer polymerization); aldehydes withtriarylalkylphosphonium salts (Wittig polymerization)) are polymerizedwith addition of a base. In general, these preparation processes aredescribed, for example, in DD 84272, H. Hörhold et al., Makromol. Chem,Macromol. Symp. 12, 1987, 229-258 and H. Horhold et al., Z. Chem. 27,1987, 126.

Cyano-substituted poly(triptycenylvinylenes) can be prepared by theKnoevenagel reaction. In this, a bis-cyanomethyl-substituted aromaticcompound is reacted with a dialdehyde with addition of a base (see, forexample, H. Hörhold et al., Plaste und Kautschuk 17, 1970, 84).

For the preparation of copolymers, triptycene or heterotriptycenemonomers can be polymerized together with one or more comonomers, asdescribed, for example, in “Makromolekuile” [Macromolecules] byHans-Georg Elias (Hüthig & Wepf Verlag Basle-Heidelberg-New York), pp.32-40.

The polymers according to the invention can be worked up by knownmethods which are familiar to the person skilled in the art, asdescribed, for example, in D. Braun, H. Cherdron, W. Kem, Praktikum dermakromolekularen organischen Chemie [Practical Macromolecular OrganicChemistry], 3rd Edn. Hüthig Verlag, Heidelberg, 1979, pp. 87-89 or R. J.Young, P. A. Lovell, Introduction to Polymers, Chapman & Hall, London1991. For example, the reaction mixture can be filtered, diluted withaqueous acid, extracted and the crude product obtained after drying andstripping-off of the solvent can be further purified by reprecipitationfrom suitable solvents with addition of precipitants. Polymer-analogousreactions can subsequently be carried out for further functionalizationof the polymer. Thus, for example, terminal halogen atoms can be removedreductively by reduction with, for example, LiAlH₄ (see, for example, J.March, Advanced Organic Chemistry, 3rd Edn. McGraw-Hill, p. 510).

The polymers according to the invention are suitable for use aselectroluminescent materials.

For the purposes of the present invention, the term “electroluminescentmaterials” is taken to mean materials which can be used as or in anactive layer in an electroluminescent device. The term “active layer”means that the layer is capable of emitting light (light-emitting layer)on application of an electric field and/or that it improves theinjection and/or transport of the positive and/or negative charges(charge injection or charge transport layer). In addition, the use aselectron-blocking layer or hole-blocking layer is a use according to theinvention.

The invention therefore also relates to the use of the polymersaccording to the invention as electroluminescent material. The inventionfurthermore relates to an electroluminescent material which comprisesthe polymers according to the invention.

In order to be used as electroluminescent materials, the polymersaccording to the invention are generally applied in the form of a filmto a substrate by known methods familiar to the person skilled in theart, such as dipping, spin coating, vapor deposition or buffering-outunder reduced pressure.

The invention likewise relates to an electroluminescent device havingone or more active layers, where at least one of these active layerscomprises one or more polymers according to the invention. The activelayer can be, for example, a light-emitting layer and/or acharge-transport layer and/or a charge-injection layer. The generalconstruction of electroluminescent devices of this type is described,for example, in U.S. Pat. No. 4,539,507 and U.S. Pat. No. 5,151,629.

They usually contain an electroluminescent layer between a negativeelectrode and a positive electrode, where at least one of the electrodesis transparent for part of the visible spectrum. In addition, one ormore electron-injection and/or electron-transport layers can beintroduced between the electroluminescent layer and the negativeelectrode and/or one or more hole-injection and/or hole-transport layerscan be introduced between the electroluminescent layer and the positiveelectrode. Suitable negative electrodes are preferably metals or metalalloys, for example Ca, Mg, Al, In or Mg/Ag. The positive electrodes canbe metals, for example Au, or other metallically conducting substances,such as oxides, for example ITO (indium oxide/tin oxide) on atransparent substrate, for example made of glass or a transparentpolymer.

In operation, the negative electrode is set to a negative potentialcompared with the positive electrode. Electrons are injected by thenegative electrode into the electron-injection layer/electron-transportlayer or directly into the light-emitting layer. At the same time, holesare injected by the positive electrode into the hole-injectionlayer/hole-transport layer or directly into the light-emitting layer.

The injected charge carriers move through the active layers toward oneanother under the effect of the applied voltage. This results inelectron/hole pairs recombining at the interface between thecharge-transport layer and the light-emitting layer or within thelight-emitting layer with emission of light. The color of the emittedlight can be varied by means of the materials used as light-emittinglayer.

Electroluminescent devices are used, for example, as self-illuminatingdisplay elements, such as control lamps, alphanumeric displays, signsand in opto-electronic couplers.

Compounds of the formula (I) are furthermore suitable, for example, foruse in optical storage media, as photorefractive materials, fornonlinear-optical (NLO) applications, as optical brighteners andradiation converters and, preferably, as hole-transport materials inphotovoltaic cells, as described, for example, in WO-A 97/10 617 andDE-A 197 11 713, to which reference is made for these applications.

The polymers according to the invention have excellent solubility inorganic solvents. The film-forming properties are excellent comparedwith poly(p-phenylene). Particular emphasis should be placed on thetemperature stability of the emission color, i.e. the fact that themorphology of the polymer is not destroyed with thermal activation.Furthermore, high charge carrier mobilities are observed.

The invention is explained in greater detail by the examples belowwithout being restricted thereby.

EXAMPLES

Polymer LEDs were produced by the general process outlined below.Naturally, this had to be adapted to the particular circumstances (forexample polymer viscosity and optimum layer thickness of the polymer inthe device and the like) in individual cases. The LEDs described belowwere in each case one-layer systems, i.e.substratel//ITO//polymerl//negative electrode.

General process for the production of high-efficiency long-life LEDsusing triptycene-containing polymers:

After the ITO-coated substrates (for example glass support, PET foil)had been cut to the correct size, they were cleaned in a number ofcleaning steps in an ultrasound bath (for example, soap solution,Millipore water, isopropanol). For drying, they were blown with an N₂gun and stored in a desiccator. Before coating with the polymer, theywere treated with an ozone plasma unit for about 20 minutes. A solutionof the respective polymer (in general with a concentration of 4-25 mg/mlin, for example, toluene, chlorobenzene, xylene:cyclohexanone (4:1)) wasprepared and dissolved by stirring at room temperature. Depending on thepolymer, it may also be advantageous to stir the solution at 50-70° C.for some time. When the polymer had dissolved completely, it wasfiltered through a 5 gm filter and coated on at variable speeds(400-6000 r.p.m.) using a spin coater. It was possible to vary the layerthicknesses thereby in the range from about 50 to 300 nm. Electrodeswere subsequently applied to the polymer films. This was generallycarried out by thermal evaporation (Balzer BA360 or Pfeiffer PL S 500).The transparent ITO electrode was then connected as positive electrodeand the metal electrode (for example Ca) as negative electrode, and thedevice parameters were determined.

Example M1 Synthesis of Dihydrotriptycene-1,4-quinone

17.8 g (100 mmol) of anthracene and 10.8 g (100 mmol) of p-benzoquinone(freshly sublimed) were dissolved in 200 ml of p-xylene at 135° C. undernitrogen. After a few minutes, the red-colored solution began to deposita yellow, crystalline precipitate. After 4 hours, the mixture wasallowed to cool to room temperature, and the precipitate was filteredoff with suction. The yellow solid was rinsed with p-xylene and driedunder reduced pressure. The resultant 26.0 g (91 mmol, 91% yield) wereheated to 130° C. in 100 ml of p-xylene under N₂, and this temperaturewas maintained for 0.5 hour, the mixture was cooled to room temperature,and the product was filtered off with suction, rinsed with methanol anddried, giving 23.5 g (82 mmol, 82% yield) ofdihydrotriptycene-1,4-quinone as pale yellow crystals.

Melting point: 232° C.

¹H NMR: (400 MHz; CDCl₃): [ppm]=3.15 (t, 2H, tert. H), 4.86 (s, 2H, enylH), 6.30 (s, 2H, bridgehead H) 7.07 and 7.39 (4H, m, J=5.3 Hz, 2.3Hz-phenyl H), 7.17-7.20 ppm, m, 4H, phenyl H).

Example M2 Synthesis of 1,4-Triptycene-1,4-quinone

37.0 g (129 mmol) of dihydrotriptycene-1.4-qione were suspended in 350ml of glacial acetic acid, and 1.5 ml of HBr (48% strength in water)were added at the boil. The mixture was refluxed for 2 hours. A solutionof 13.0 g of KIO₃ (60 mmol) was then added dropwise at the boil over thecourse of 5 minutes. A yellow coloration of the suspension wasimmediately evident. The mixture was allowed to cool, 200 ml of waterwere added at 50° C., and the solid was filtered off with suction, thenwashed a number of times with Na₂SO₃ solution and subsequently a numberof times with water and dried under reduced pressure. The crude product(35.2 g, 96% yield) was triturated twice for one hour each time in 150ml of isopropanol, giving 30.9 g (108.7 mmol, 84% yield) of1,4-triptycene-1,4-quinone as a luminescent-yellow powdery substance.

Melting point: 273-275° C. ¹H NMR: (400 MHz; CDCl₃): [ppm]=5.79 (s, 2H,bridgehead H), 6.59 (s, 2H, enyl H), 7.03 and 7.42 (m, 8H, J=2.3 Hz, 5.3Hz, AB system phenyl H).

Example M3 Synthesis of 1,4-Dihydroxy-1,4-dimethyltriptycene

148 ml (237 mmol, 2.7 eq) of a 1.6 M solution of methyllithium indiethyl ether were introduced into a 1 l four-necked flask together with300 ml of THF (distilled from Na/benzophenone) and cooled to −78° C.(acetone/dry ice). At the same time, a solution of 25.0 g (87.9 mmol) of1,4-triptycene-1,4-quinone in 600 ml of THF was cooled to the sametemperature. The solution of 1,4-triptycene-1,4-quinone was transferredinto a dropping funnel, which was additionally cooled by means of dryice. The starting-material solution was slowly added dropwise (1 hour)with vigorous stirring, the solution immediately changing color fromblue to blue-green. When the addition was complete, the temperature wasmaintained for a further hour, and the cooling was subsequently removed.The mixture was allowed to warm to room temperature and was stirredovernight. The suspension was evaporated to about 200 ml under reducedpressure and subsequently poured into a mixture of 1.4 L of ice-water on10 g of NH₄Cl. During the pouring-in, heat was evolved and a pale beigeprecipitate deposited, which liquified on warming to room temperature.The resultant oil was separated off, and the water phase was extractedthree times with 500 ml of CH₂Cl₂. The combined organic phases werewashed twice with 200 ml of water each time, dried using Na₂SO₄ andevaporated as far as possible on a rotary evaporator.

A brown, viscous material remained which was treated with 30 ml ofdiethyl ether/hexane 2:1 in an ultrasound bath until all the oil haddissolved and a white precipitate had formed. The precipitate wasfiltered off with suction, and the mother liquor was again evaporated ina rotary evaporator and treated in the same way, the volumes ofEt₂O/hexane mixture being chosen somewhat smaller each time. Theoperation was repeated until no further precipitate deposited. Forfurther purification, the reaction mixture was refluxed in diethylether, cooled to 20° C. and filtered off with suction, giving 14.9 g(47.1 mmol, 54%) of 1,4-dihydroxy-1,4-dimethyltriptycene as a whitepowder.

¹H NMR: (400 MHz; DMSO-d₆):=1.09 (s, 6H, methyl H); 4.84 (s, 2H, hydroxyH); 5.34 (s, 2H, quinone H); 5.63 (s, 2H, bridgehead H); 6.90, 6.92,7.28, 7.33 (m, each 2H, J=5.3 Hz and 2.3 Hz, phenyl H). ¹H NMR: (400MHz; CDCl₃):=1.27 (s, 6H, methyl H); 1.63 (s, 2H, hydroxy H); 5.39 (s,2H, quinone H); 5.54 (s, 2H, bridgehead H); 6.91 (m, 2H, J=5.5 Hz and2.3 Hz, phenyl H); 6.95 m, 2H, J=5.3 Hz and 2.0 Hz, phenyl H); 7.32 (m,4H, J=5.3 Hz, 2.3 Hz and 2.0 Hz, phenyl H).

Example M4 Synthesis of 1.4-Dimethyltriptycene

6.70 g (53.3 mmol, 2.1 eq) of SnCl₂.2 H₂O were dissolved in 200 ml of50% strength acetic acid. A methanolic solution of 8.44 g (25.7 mmol) of1,4-dihydroxy-1,4-dimethyltriptycene was slowly added dropwise theretoat such a rate that the temperature did not rise higher than a maximumof 45° C. The reaction solution adopted a yellowish coloration, and awhite precipitate deposited. When the addition was complete, the mixturewas stirred at room temperature for a further 2 hours and then cooled to−18° C., and the resultant precipitate was filtered off with suction,washed with about 1 L of water until acid-free and dried under reducedpressure. The resultant mother liquor was then evaporated somewhat in arotary evaporator, and the precipitate which deposited on re-cooling wasagain filtered off with suction, giving 7.0 g of crude product. Thecompound was dissolved in about 300 ml of acetone at the boil andsubsequently precipitated with 50 ml of water. The solution was cooledin the ice compartment, and the precipitate was filtered off withsuction. Repetition of the procedure gave 5.20 g (18.4 mmol, 72%) of1,4-dimethyltriptycene as white sparkling crystals.

Melting point: 246-249° C. ¹H NMR: (400 MHz; DMSO-d₆):=2.43 (s, 6H,methyl H); 5.80 (s, 2H, bridgehead H); 6.71 (s, 2H, phenyl H); 6.98 and7.45 (m, 8H, J=2.3 Hz, 5.3 Hz, AB system, phenyl H). ¹H NMR: (400 MHz;CDCl₃):=2.46 (s, 6H, methyl H); 5.64 (s, 2H, bridgehead H); 6.70 (s, 2H,phenyl H); 6.97 and 7.36 (m, 8H, J=2.3 Hz, 5.3 Hz, AB system, phenyl H).

Example M5 Synthesis of 1,4-bis(Bromomethyl)triptycene

5.20 g (18.4 mmol) of 1,4-dimethyltriptycene were dissolved in 150 ml ofdry tetrachloromethane, and 3.45 g (19.3 mmol) of N-bromosuccinimide and0.20 g (1.22 mmol) of diazoisobutyronitrile were added. The suspensionwas heated under a gentle reflux with irradiation with light. Themixture was allowed to react for one hour. After checking by TLC(hexane/CH₂Cl₂1:1), N-bromosuccinimide was added until the spot betweenthe starting material and product had disappeared. The mixture was thenallowed to cool, and the succinimide was separated off by filtration.The reaction solution was evaporated as far as possible (30 ml) in arotary evaporator, a little hexane was added, and the mixture wascooled. The precipitate was filtered off with suction and dried, giving7.70 g (17.5 mmol, 95%) of pale-yellow crude product. For purification,the product was recrystallized from glacial acetic acid, giving 5.6 g(12.7 mmol, 70%) of 1,4-bis(bromomethyl)triptycene as colorlesscrystals.

Melting point: 198-208° C. ¹H NMR: (400 MHz; CDCl₃):=4.67 (s, 4H,bromomethyl H); 5.40 (s, 2H, bridgehead H), 6.90 (s, 2H, phenyl H); 7.02and 7.47 (m, J=5.3 Hz, 3.3 Hz, 8H, AB system, phenyl H).

Example P1 Copolymer of 80% of2,5-bis(Chloromethyl)-1-methoxy-4-(3,7-dimethyloctyloxy)benzene and 20%of 1,4-bis(Bromomethyl)triptycene (Polymer 1)

720 ml of dry and O₂-free 1,4-dioxane were heated to 95° C. in a dry 2 Lfour-necked flask fitted with mechanical Teflon stirrer, refluxcondenser, thermometer and dropping funnel. A solution 2.89 g (8 mmol)of 2,5-bis(chloromethyly-1-methoxy-4-(3′,7′-dimethyloctyloxy)benzene and880 mg (2 mmol) of 1,4-bis(bromomethyl)triptycene in 10 ml of dry1,4-dioxane were then added. A solution of 2.92 g (26 mmol) of potassiumtert-butoxide in 25 ml of dry 1,4-dioxane was then added dropwise to thevigorously stirred mixture over the course of 5 minutes. During thisoperation, the color changed from colorless via yellow to orange-red.After 5 minutes, a further 2.24 g (20.0 mmol) of potassiumtert-butoxide, dissolved in 20 ml of 1,4-dioxane, were added. After themixture had been stirred at 95-97° C. for 2 hours, it was cooled to 55°C., and a mixture of 4 ml of acetic acid and 4 ml of 1,4-dioxane wasadded. The solution, which was now orange, was poured into 1 L ofvigorously stirred water. The precipitated polymer was isolated byfiltration through a polypropylene filter and dried under reducedpressure. The crude yield was 2.50 g (8.7 mmol, 87%).

The polymer was dissolved in 330 ml of THF with heating to 60° C. andprecipitated by addition of 330 ml of methanol at 40° C. After dryingunder reduced pressure, this step was repeated. Drying under reducedpressure gave 1.46 g (=5.10 mmol, 51%) of polymer 1 as pale-orangefibers.

The content of triptycene groups was determined by ¹H-NMR spectroscopy.To this end, the signal of the triptycene bridgehead H atoms (6.0 ppm)was integrated and compared with the OCH₃ and OCH₂ signals at 4.2-3.6ppm; 9% of triptycene units were determined in the polymer.

¹H-NMR (400 MHz, CDCb₃): (ppm)=7.9-6.6 (broad multiplet, 5.6 H; aryl H,olefin H); 6.0 (broad singlet; 0.4H; triptycene bridgehead H); 4.2-3.6(br. m [?], 4H; OCH₂, OCH₃); 2.0-0.9 (broad multiplet, 9.6H; aliphaticside chain); 0.89, 0.86 (2 singlets, 7.2H; 3×CH₃). GPC: THF+0.25% oxalicacid; column set SDV500, SDV1000, SDV10000 (PSS), 35° C., UV detection254 nm, polystyrene standard: M_(w)=3.0 10⁵ g/mol, M_(n)=4.5 10⁴ g/mol.

Electroluminescence measurement: 0.34% maximum quantum efficiency at 5.2V, a luminance of 100 cd/ml was achieved at 6.81 V, 15.07 mA/cm².

Example P2 Copolymer of 91% of2,5-bis(Chloromethyl)-1-methoxy-4-(3,7-dimethyloctyloxy)benzene and 9%of 1,4-bis(Bromomethyl)triptycene (Polymer 2)

1000 ml of dry and O₂-free 1,4-dioxane were heated to 88-90° C. in a dry2 L four-necked flask fitted with precision-glass stirrer, refluxcondenser, thermometer and dropping funnel. A solution 4.34 g (12 mmol)of 2,5-bis(chloromethyl)-1-methoxy-4-(3′,7′-dimethyloctyloxy)benzene and528 mg (1.2 mmol) of 1,4-bis(bromomethyl)-triptycene in 20 ml of dry1,4-dioxane were then added. A solution of 3.85 9 (34.3 mmol) ofpotassium tert-butoxide in 34 ml of dry 1,4-dioxane was then addeddropwise to the reaction mixture over the course of 5 minutes withvigorous stirring. During this operation, the color changed fromcolorless via yellow to orange-red. After 5 minutes, a further 3.85 g(34.3 mmol) of potassium tert-butoxide, dissolved in 26 ml of1,4-dioxane, were added. After the mixture had been stirred at 88° C.for 2 hours, it was cooled to 55° C., and 12 ml of a 1,4-dioxane/glacialacetic acid 1:1 mixture were added. The viscous solution, which was noworange, was poured into 1 L of vigorously stirred water. Theprecipitated polymer was isolated by filtration through a polypropylenefilter and dried under reduced pressure. 3.4 g of crude polymer wereobtained.

The polymer was dissolved in 450 ml of THF with heating to 60° C. andprecipitated by addition of 560 ml of methanol at a temperature of <40°C. After drying under reduced pressure, this step was repeated. Dryingunder reduced pressure gave 2.60 g (=9.03 mmol, 68%) of polymer 2 aspale-orange fibers. The content of triptycene groups was determined by¹H-NMR spectroscopy. To this end, the signal of the triptycenebridgehead H (6.0 ppm) was integrated and compared with the OCH₃ andOCH₂ signals at 4.2-3.6 ppm; 3.5% of triptycene units were determined inthe polymer.

¹H-NMR (400 MHz, CDCl₃): (ppm)=7.9-6.6 (broad multiplet, 4H; aryl H,olefin H); 6.0 (broad singlet; add. 0.02H; triptycene bridgehead H);4.2-3.6 (br. m, 5H; OCH₂, OCH₃); 2.0-0.9 (broad multiplet, 10H;aliphatic side chain); 0.89, 0.86 (2 singlets, 9H; 3×CH₃). GPC:THF+0.25% oxalic acid; column set SDV500, SDV1000, SDV10000 (PSS), 35°C., UV detection 254 nm, polystyrene standard: M_(w)=2.0 105 g/mol,M_(n)=3.1 10⁴ g/mol.

Electroluminescence measurement: 0.21% maximum quantum efficiency at 5.2V, a luminance of 100 cd/m² was achieved at 5.05 V, 11.17 mA/cm².

Copolymer of 80% of2,5-bis(chloromethyl)3′-(3,7-dimethyloctyloxy)biphenyl and 20% of1,4-bis(bromomethyl)triptycene (polymer 3):

0.72 kg of dry and O₂-free 1,4-dioxane were introduced into a dry 2 Lfour-necked flask fitted with mechanical stirrer, reflux condenser,thermometer and dropping funnel and heated to 98° C. with stirring. Asolution of 3.26 g (8 mmol) of2,5-bis(chloromethyl)-3′(3,7-dimethyloctyloxy)biphenyl and 0.88 g (2mmol) of 1,4-bis(bromomethyl)triptycene, dissolved in 30 ml of dry1,4-dioxane, was then added. A solution of 2.87 g (26 mmol, 2.6equivalents) of potassium tert-butoxide in 26 ml of dry 1,4-dioxane wasthen added dropwise to the vigorously stirred mixture over the course of5 minutes. During this operation, the color changed from colorless viagreen to pale orange; the viscosity of the solution increased slightly.After the mixture had been stirred at 98° C. for 5 minutes, a further2.24 g (20 mmol, 2.0 equivalents) of potassium tert-butoxide in 20 ml of1,4-dioxane were added over the course of one minute. After the mixturehad been stirred at 95-98° C. for a further 2 hours, it was cooled to50° C., and a mixture of 4 ml of acetic acid and 4 ml of 1,4-dioxane wasadded. After the mixture had been stirred for a further 20 minutes, thepolymer was precipitated by addition of the reaction solution to 0.7 Lof vigorously stirred water. The resultant polymer was filtered off andwashed twice with 100 ml of methanol each time. Drying at roomtemperature under reduced pressure gave 3.17 g (9.8 mmol, 98%) of crudepolymer 3.

The crude product was dissolved in 400 ml of THF with heating to 60° C.and precipitated by addition of 400 ml of methanol. After the producthad been dried under reduced pressure and washed with 100 ml ofmethanol, this step was repeated. Drying for 2 days under reducedpressure gave 1.84 g (=5.7 mmol, 57%) of polymer 3 as pale-orangefibers.

The content of triptycene groups was determined by ¹H-NMR spectroscopy.To this end, the signal of the triptycene bridgehead H (5.9 ppm) wasintegrated and compared with the OCH₂ signal at 4.0 ppm; 14% oftriptycene units were present in the polymer.

¹H-NMR (400 MHz, CDCl₃): (ppm)=7.9-6.1 (broad multiplet, 9.2H; aryl andolefin H); 5.9 (broad singlet; 0.28H; triptycene bridgehead H); 4.0(broad singlet, 1.6H); 1.95-0.85 (broad multiplet, 15.2H; aliphatic H).GPC: THF+0.25% oxalic acid; column set SDV500, SDV1000, SDV10000 (PSS),35° C., UV-detection 254 nm, polystyrene standard: M_(w)=4.4 10⁵ g/mol,M_(n)=9.1 10⁴ g/mol.

Electroluminescence measurement: 0.47% maximum quantum efficiency at10.7 V, a luminance of 100 cd/M² was achieved at 10.9 V._(max)=517 nm.

Example P4 Copolymer of 75% of2,5-bis(Chloromethyl-1-methoxy-4-(3,7-dimethyloctyloxy)benzene and 25%of 1,4-bis(Bromomethyl)triptycene (polymer 4)

385 ml of dry and O₂-THF were introduced into a dry 500 ml four-neckedflask fitted with mechanical Teflon stirrer, reflux condenser,thermometer and dropping funnel. 1.58 g (3.6 mmol) of2,5-bis(bromomethyl)-1-methoxy4-(3′,7′-dimethyloctyloxy)benzene and 528mg of (1.2 mmol) of 1,4-bis(bromomethyl)triptycene were then added. Asolution of 1.32 g (11.8 mmol) of potassium tert-butoxide in 12 ml ofdry THF was then added dropwise to the vigorously stirred mixture overthe course of 5 minutes. During this operation, the color changed fromcolorless via yellow to orange-red. After 5 minutes, a further 1.1 g(9.8 mmol) of potassium tert-butoxide, dissolved in 10 ml of THF, wereadded in one portion. After the mixture had been stirred at roomtemperature for 2 hours, it was heated at 60° C. for one hour, and amixture of 2 ml of acetic acid and 2 ml of 1,4-dioxane was added. Thesolution, which was now orange, was poured into 1 L of vigorouslystirred water. The precipitated polymer was isolated by filtrationthrough a polypropylene filter and dried under reduced pressure. Thecrude yield was 1.2 g. The polymer was dissolved in 160 ml of THF withheating to 60° C. and precipitated by addition of 200 ml of methanol atroom temperature. After drying under reduced pressure, this step wasrepeated. Drying under reduced pressure gave 0.89 g (=2.98 mmol, 62%) ofpolymer 4 as pale-orange fibers.

The content of triptycene groups was determined by ¹H-NMR spectroscopy.To this end, the signal of the triptycene bridgehead H (6.0 ppm) wasintegrated and compared with the OCH₃ and OCH₂ signals at 4.2-3.6 ppm;15% of triptycene units were determined in the polymer.

¹H-NMR (400 MHz, CDCl₃): (ppm)=7.9-6.6 (broad multiplet, 4H; aryl H,olefin H); 6.0 (broad singlet; 0.3 additional H; triptycene bridgeheadH); 4.2-3.6 (broad multiplet, 5H); OCH₂, OCH₃); 2.0-0.9 (broadmultiplet, 10H; aliphatic side chain); 0.89, 0.86 (2 singlets, 9H;3×CH₃). GPC: THF+0.25% oxalic acid; column set SDV500, SDV1000, SDV10000(PSS), 35° C., UV detection 254 nm, polystyrene standard: M_(w)=3.0 10⁵g/mol, M_(n)=4.5 10⁴g/mol. Electroluminescence measurement: 0.96%maximum quantum efficiency at 6.01 V, a luminance of 100 cd/m² wasachieved at 4.11 V/1 6.07 mA/cm².

What is claimed is:
 1. A conjugated polymer comprising a) from 1 to 100mol % of at least one recurring unit RU1 of the formula (I)—B—Tr—A—  (I) in which Tr is a triptycenylene radical of the formula(II)

or of the formula (III)

or of the formula (IV)

wherein R¹ to R¹⁶ are identical or different and are H; linear orbranched C₁-C₂₂-alkyl in which one or more non-adjacent CH₂ groups areoptionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amidegroup and in which one or more H atoms are optionally replaced by Fatoms; linear or branched C₁-C₂₂-alkoxy, in which one or morenon-adjacent CH₂ groups are optionally replaced by —O—, —S—, —CO—,—COO—, —O—CO—, an amino or amide group and in which one or more H atomsare optionally replaced by F atoms, C₆-C₂₀-aryl, C₆-C₂₀-aryloxy, COOR,SO₃R, CN, halogen or NO₂, G, L, and where appropriate G¹ and L¹ areidentical or different and are CR¹⁷, N, P or As and R¹⁷ is H,C₁-C₂₂-alkyl in which one or more non-adjacent CH₂ groups are optionallyreplaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amide group andin which one or more H atoms are optionally replaced by F atoms,C₁-C₂₂-alkoxy, in which one or more non-adjacent CH₂ groups areoptionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amidegroup and in which one or more H atoms are optionally replaced by Fatoms, C₆-C₂₀-aryl, halogen or CN, A and B are identical or differentand are a single bond, a vinylene radical which is optionallysubstituted by H, linear or branched C₁-C₂₂-alkyl in which one or morenon-adjacent CH₂ groups is optionally replaced by —O—, —S—, —CO—, —COO—,—O—CO—, an amino or amide group and in which one or more H atoms areoptionally replaced by F atoms, linear or branched C₁-C₂₂-alkoxy, inwhich one or more non-adjacent CH₂ groups is optionally replaced by —O—,—S—, —CO—, —COO—, —O—CO—, an amino or amide group and in which one ormore H atoms are optionally replaced by F atoms, or C₆-C₂₀-aryl,C₆-C₂₀-aryloxy, C₃-C₂₀-heteroaryl, COOR, SO₃R, CN, halogen, NO₂, amino,alkylamino, dialkylamino, an ethynylene radical, an arylene radical ofthe formula V

where R¹⁸ to R²¹ are identical or different and are as defined above forR¹ to R¹⁶, a heteroarylene radical of the formula (VI)

X and Y are identical or different and are N or CR²², and Z is O, S,NR²³, CR²⁴R²⁵, CR²⁶=CR²⁷ or CR²⁸=N—, in which R²² to R²⁸ are ordifferent and are as defined above for R¹ to R ¹⁶, or aspirobifluorenylene radical of the formula (VII)

where R²⁹ to R³² are identical or different and are as defined above forR¹ to R¹⁶, and b) from 0 to 99 mol % of at least one recurring unit RU2of the formula (VIII)

where R³³ to R³⁶ are identical or different and are as defined above forR¹ to R¹⁶, or of the formula (IX)

where X, Y and Z are as defined above, and D is a single bond, avinylene radical which is optionally substituted by H, linear orbranched C₁-C₂₂-alkyl in which one or more non-adjacent CH₂ groups areoptionally replaced by —O—, —S—, —CO—, —COO—, —O—CO—, an amino or amidegroup and in which one or more H atoms are optionally replaced by Fatoms, linear or branched C₁-C₂₂-alkoxy, in which one or morenon-adjacent CH₂ groups are optionally replaced by —O—, —S—, —CO—,—COO—, —O—CO—, an amino or amide group and in which one or more H atomsare optionally replaced by F atoms, C₆-C₂₀-aryl C₆-C₂₀-aryloxy,C₃-C₂₀-heteroaryl, COOR, SO₃R, CN, halogen, NO₂, amino, alkylamino,dialkylamino, or an ethynylene radical.
 2. The polymer as claimed inclaim 1, in which L and G and optionally L¹ and G¹ are a CH group. 3.The polymer as claimed in claim 1, which is a homopolymer comprisingrecurring units RU1.
 4. The polymer according to claim 3, wherein A isselected from the group consisting of 2,5-thiophenylene,2,5-oxadiazolylene, 1,4-phenylene, vinylene and ethynylene, and B is asingle bond.
 5. The polymer according to claim 3, wherein A and B areidentical and are selected from the group consisting of2,5-thiophenylene, 1,4-phenylene, vinylene and ethynylene.
 6. Thepolymer according to claim 1, comprising from 1 to 99 mol % of recurringunits RU2.
 7. The polymer according to claim 6, wherein A is a singlebond and B is a single bond, a vinylene group or an ethynylene group. 8.The polymer according to claim 7, wherein B is a vinylene group.
 9. Thepolymer according to claim 6, wherein the polymer is a binary copolymercomprising recurring units RU1 and recurring units RU2 of the formula(VIII) or (IX).
 10. The polymer according to claim 6, which the polymeris a ternary copolymer comprising recurring units RU1 and two types ofrecurring units RU2 of the formula (VIII) or (IX).
 11. The polymeraccording to claim 10, wherein the recurring units RU2 are recurringunits of the formula (VIII).
 12. The polymer according to claim 10,wherein D is a vinylene group.
 13. An electroluminescent materialcomprising the polymer as claimed in claim
 1. 14. A process for thepreparation of an electroluminescent material which comprises applyingthe polymer as claimed in claim 1 in the form of a film to a substrate.15. An electroluminescent device which comprises one or more activelayers, where at least one of these active layers comprises the polymeras claimed in claim 1.